Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

8. Elimination Reactions

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

Organic Chemistry

8. Elimination Reactions

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

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4:30 minutes

Problem 6b

Textbook Question

A small amount of another organic product is formed in a Williamson ether synthesis. What is this product when the alkyl halide used in the synthesis of butyl propyl ether is
b. butyl bromide?

Verified step by step guidance

Understand the Williamson ether synthesis: This reaction involves the reaction of an alkoxide ion (R-O⁻) with an alkyl halide (R'-X) to form an ether (R-O-R'). However, side reactions can occur, especially elimination reactions.

Identify the reactants: In this case, the alkyl halide is butyl bromide (CH₃CH₂CH₂CH₂Br), and the alkoxide ion is propoxide (CH₃CH₂CH₂O⁻), which will form the main product, butyl propyl ether (CH₃CH₂CH₂OCH₂CH₂CH₂CH₃).

Consider the side reaction: The alkyl halide (butyl bromide) can undergo an elimination reaction in the presence of a strong base like the alkoxide ion. This elimination reaction follows the E2 mechanism, where the base abstracts a β-hydrogen from the alkyl halide, leading to the formation of an alkene.

Determine the product of elimination: In the case of butyl bromide, the β-hydrogen is removed, and the double bond forms between the α and β carbons, resulting in 1-butene (CH₂=CHCH₂CH₃) as the side product.

Summarize the side product: The small amount of side product formed in this Williamson ether synthesis is 1-butene, which arises from the E2 elimination of butyl bromide.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Williamson Ether Synthesis

Williamson ether synthesis is a method for creating ethers through the reaction of an alkoxide ion with a primary alkyl halide. This reaction typically involves nucleophilic substitution, where the alkoxide acts as a nucleophile, attacking the electrophilic carbon of the alkyl halide, resulting in the formation of an ether and a halide ion.

Alkyl Halides

Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (such as bromine, chlorine, or iodine). In the context of Williamson ether synthesis, the choice of alkyl halide is crucial, as primary alkyl halides favor the desired nucleophilic substitution reaction, while secondary or tertiary halides may lead to elimination reactions instead.

Side Products in Reactions

In organic reactions, side products can form alongside the desired product due to competing reaction pathways. In the case of Williamson ether synthesis, when butyl bromide is used, a common side product is the formation of butane, which occurs if the alkyl halide undergoes elimination instead of substitution, highlighting the importance of reaction conditions and substrate choice.

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Related Practice

Textbook Question

For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.

c. trans-1-chloro-2-methylcyclohexane + high concentration of CH₃O⁻

Textbook Question

What product is formed when 1-bromopropane reacts with each of the following nucleophiles?

d. HS⁻

Textbook Question

What product is formed when 1-bromopropane reacts with each of the following nucleophiles?

c. CH₃S⁻

Textbook Question

Identify the three products formed when 2-bromo-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.

Textbook Question

A small amount of another organic product is formed in a Williamson ether synthesis. What is this product when the alkyl halide used in the synthesis of butyl propyl ether is

a. propyl bromide?

Textbook Question

Draw the elimination products that are formed when 3-bromo-3-methyl-1-butene reacts with

b. CH₃OH

Textbook Question

Draw the elimination products that are formed when 3-bromo-3-methyl-1-butene reacts with

a. CH₃O⁻.

Textbook Question

For each of the following reactions, (1) decide whether an E2 or an E1 occurs, and (2) draw the major elimination product:

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A small amount of another organic product is formed in a Williamson ether synthesis. What is this product when the alkyl halide used in the synthesis of butyl propyl ether is b. butyl bromide?

Key Concepts

Williamson Ether Synthesis

Alkyl Halides

Side Products in Reactions

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A small amount of another organic product is formed in a Williamson ether synthesis. What is this product when the alkyl halide used in the synthesis of butyl propyl ether is
b. butyl bromide?